68430-29-5Relevant academic research and scientific papers
Convenient Preparation Procedure for (5S)-5-Hydroxymethyloxazolidin-2-ones, Universal Precursors of Adrenoblocking Compounds
Bredikhin,Bredikhina
, p. 532 - 535 (2007/10/03)
(5S)-5-Hydroxymethyl-3-alkyloxazolidin-2-ones and their tosylates, universal intermediates in the synthesis of nonracemic β-adrenoblocking compounds, were prepared from D-mannitol along a procedure increasing the effectivity of mannitol utilization and reducing the number of steps leading to the target products.
Method of preparing a heterocyclic intermediate for the production of optically active aryloxysubstituted vicinal aminoalcohols
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, (2008/06/13)
The invention relates to a method of preparing a heterocyclic intermediate of the general formula wherein, X is a carbonyl group, a thiocarbonyl group, a (C1-C10)(ar)alkylidene group or a dihydrocarbylsilyl group, R is a straight or branched (C1-C10)alkyl group, optionally substituted with halogen, hydroxy, (C1-C4)alkoxy or protected hydroxy, or a phenyl(C1-C3)alkyl or heteroaryl(C1-C3)alkyl group, which groups are optionally substituted with 1-3 substituents, selected from the group consisting of hydroxy, (C5-C12)cycloalkyl, amino, nitro, halogen, cyano, alkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylsulphonylamino, alkylsulphonyl, alkylcarbonyl, and alkyl, wherein the alkyl groups have 1-5 carbon atoms,and which intermediate has either the R or the S configuration, by subjecting an optically active cyanohydrin of the general formula to a reduction-transimination-reduction sequence, using R - NH2 as the primary amine,followed by a cyclization reaction and, finally, by an ozonolysis-reduction sequence.
Synthesis of (R)- and (S)-5-(hydroxymethyl)-3-isopropyloxazolidin-2-one, intermediates in the preparation of optically active β-blockers
Warmerdam,Brussee,Van Der Gen,Kruse
, p. 252 - 256 (2007/10/02)
The (R)- and (S)-5-(hydroxymethyl)-3-isopropyloxazolidin-2-ones, ((R)- and (S)-2, resp.), pivotal intermediates in the preparation of optically active β-blockers, were synthesized using (R,E)-2-hydroxypent-3-enenitrile (1) as the chiral starting material.
CHIRAL AMINO ALCOHOLS FROM BAKER'S YEAST REDUCTION OF α-KETO-ACID DERIVATIVES
Pedrocchi-Fantoni, Giuseppe,Redaelli, Silvio,Servi, Stefano,Hoegberg, Hans-Erik
, p. 499 - 502 (2007/10/02)
Baker's yeast reduction of α-keto-acid derivatives gives α-hydroxy esters and amides of varying enantiomeric excesses.In the case of the keto amide, an amino alcohol of high optical purity is formed.The product obtained is transformed in key intermediates in the synthesis of (S)-propranolol.
Process for S-metoprolol via oxazolidin-2-one
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, (2008/06/13)
A process for preparing S-metoprolol of the formula STR1 or a salt thereof, with high enantiomeric purity, is described, whereby a (S)-5-hydroxymethyl-3-isopropyloxazolidin-2-one sulfonic acid ester of the formula STR2 is prepared, and further reacted wit
FACILE PROCESS FOR ENZYMIC RESOLUTION OF RACEMIC ALCOHOLS
Terao, Yoshiyasu,Tsuji, Keiichiro,Murata, Masakazu,Achiwa, Kazuo,Nishio, Toshiyuki,et al.
, p. 1653 - 1655 (2007/10/02)
Lipase-catalyzed esterification of a racemic alcohol with succinic anhydride has been found to proceed enantioselectively to afford succinic acid monoester, which was easily separated from non-reacting alcohol by washing with alkaline solution.This procedure provides a facile method for the optical resolution of racemic alcohols.Keywords: optical resolution; racemic alcohol; lipase; succinic anhydride; 1,3-dioxolane-4-methanol
Anhydrides as Acylating Agents in Lipase-Catalyzed Stereoselective Esterification of Racemic Alcohols
Bianchi, Daniele,Cesti, Pietro,Battistel, Ezio
, p. 5531 - 5534 (2007/10/02)
A new enzymatic method for the resolution of optically active alcohols from racemates is reported.It involves lipase-catalyzed esterification in organic solvents, with acetic, propionic, or butyric anhydrides as acylating agents.Lipase Amano P, from Pseudomonas fluorescens, adsorbed on Celite 577, was employed as stereoselective catalyst.Under these reaction conditions, the enzyme is not chemically modified by the anhydrides.A number of primary and secondary alcohols have been obtained in high optical purity by this procedure.
